Synthesis method of 6-(trifluoromethyl) isoquinoline-5-ol

A technology of trifluoromethyl isoquinoline and trifluoromethyl, which is applied in the field of synthesis of 6-(trifluoromethyl) isoquinoline-5-ol, can solve problems such as incapability of large-scale production, and achieve easy The effect of amplification, reasonable process selection and low cost of raw materials

Active Publication Date: 2020-12-18
SUZHOU KANGRUN PHARMA
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Problems solved by technology

[0003] At this stage, there is no published synthetic route of 6-(trifluoromethyl)isoquinolin-5-ol. At present, the main synthetic method of 6-trifluoromethylisoquinoline is to pass p-benzylamine under microwave Condensation reaction and sulfuri

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  • Synthesis method of 6-(trifluoromethyl) isoquinoline-5-ol

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[0041]The present invention will be further described below in conjunction with specific embodiments, but the embodiments are only exemplary and do not constitute any limitation on the scope of the present invention. Those skilled in the art should understand that the details and forms of the technical solution of the present invention can be modified or replaced without departing from the spirit and scope of the present invention, but these modifications and replacements fall within the protection scope of the present invention.

[0042] The synthesis process of 6-(trifluoromethyl)isoquinoline-5-amine of the present invention is based on m-trifluoromethylphenethylamine as a raw material, and TFAA undergoes amino protection, ring closure, hydrolysis, bromination, and debromination. And dehydroaromatization to obtain 7-trifluoromethyl isoquinoline, and NBS for 5-position bromination to produce 5-bromo-7-trifluoromethyl isoquinoline, and sodium methoxide for methoxylation and demethylat...

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Abstract

The invention discloses a synthesis method of 6- (trifluoromethyl) isoquinoline-5-ol, which comprises the following steps of by using p-trifluoromethyl phenylethylamine as a raw material, carrying outamino protection, cyclization, hydrolysis, bromination, debromination alkene insertion and dehydroaromatization on the p-trifluoromethyl phenylethylamine and TFAA to obtain 7-trifluoromethyl isoquinoline, and carrying out 5-site bromination on the 7-trifluoromethyl isoquinoline and NBS to generate 5-bromine- 7-trifluoromethyl isoquinoline, and carrying out methoxylation and demethylation with sodium methoxide to obtain 6-(trifluoromethyl) isoquinoline-5-alcohol. The method is simple in synthetic route, reasonable in process selection, low in raw material cost, simple and easily available in raw materials, convenient to operate and post-treat, high in total yield, free of highly toxic reagents and easy to amplify, and can be used for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of 6-(trifluoromethyl)isoquinolin-5-ol. Background technique [0002] 6-(Trifluoromethyl)isoquinolin-5-ol is a key pharmaceutical intermediate, and its 6-position trifluoromethyl group has excellent characteristics as a fluorine-containing substituent group. It can effectively improve bioavailability and improve pharmacokinetic properties. The 6-trifluoromethylisoquinoline structure is often used as a modification group to improve the properties of drug candidate molecules. The hydroxyl group at the 5-position can be well connected with various compounds through esterification or amidation, thereby expanding its applicability. Acharya R A et al. developed a novel aminoisoxazoline compound (WO2017069980 A1) as an α7-nicotinyl acetylcholine receptor agonist, which can improve cognitive impairment diseases such as Al...

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Application Information

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IPC IPC(8): C07D217/02
CPCC07D217/02
Inventor 晋浩文徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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